Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate → (E)-(S)-ethyl 3-{4-[3-(3',5'-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

HRID 984408Notes

Reaction equation

HRID 984408 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](/[C:15](/[CH3:19])=[CH:16]/[CH2:17][OH:18])=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:20]([O:22][C@@H:23]([CH2:29][C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12](/[C:15](/[CH3:19])=[CH:16]/[CH2:17][O:18][C:33]3[CH:32]=[CH:31][C:30]([CH2:29][C@H:23]([O:22][CH2:20][CH3:21])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:35][CH:34]=3)=[CH:13][CH:14]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 2

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 69795925(E)-3-(3',5'-dichloro-biphenyl-4-yl)-but-2-en-1-ol

Product 1

HCID 86589964(E)-(S)-ethyl 3-{4-[3-(3',5'-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionateYield 77.3%

Procedure

The title compound (794 mg, 77%) was prepared as a colourless gum from (E)-3-(3′,5′-dichloro-biphenyl-4-yl)-but-2-en-1-ol (586 mg, 2.0 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (500 mg, 2.10 mmol) by a procedure analogous to that described in example 52c.

Sources & evidence

ORD record
ord-a3de058928c847388c24bba50eebc023
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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